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Fucoxanthin

Synopsis

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Chemistry

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Also known as: 3351-86-8, All-trans-fucoxanthin, 06o0tc0vsm, Chebi:5186, (3's,5'r,6'r)-3'-acetoxy-5,6-epoxy-3,5'-dihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-beta,beta-caroten-8-one, (1s,3r)-3-hydroxy-4-((3e,5e,7e,9e,11e,13e,15e)-18-((1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene)-3,5,5-trimethylcyclohexyl acetate

Molecular Formula

C₄₂H₅₈O₆

Molecular Weight

658.9 g/mol

InChI Key

SJWWTRQNNRNTPU-ABBNZJFMSA-N

FDA UNII

06O0TC0VSM

fucoxanthin is a natural product found in Aequipecten opercularis, Ascidia zara, and other organisms with data available.

1 2D Structure

Fucoxanthin

2 Identification

2.1 Computed Descriptors

2.1.1 InChI

InChI=1S/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23?,34-,35-,40+,41+,42-/m0/s1

2.1.2 InChI Key

SJWWTRQNNRNTPU-ABBNZJFMSA-N

2.1.3 Canonical SMILES

CC(=CC=CC=C(C)C=CC=C(C)C(=O)CC12C(CC(CC1(O2)C)O)(C)C)C=CC=C(C)C=C=C3C(CC(CC3(C)O)OC(=O)C)(C)C

2.1.4 Isomeric SMILES

C/C(=C\C=C\C=C(/C)\C=C\C=C(/C)\C(=O)C[C@]12[C@](O1)(C[C@H](CC2(C)C)O)C)/C=C/C=C(\C)/C=C=C3[C@](C[C@H](CC3(C)C)OC(=O)C)(C)O

2.2 Other Identifiers

2.2.1 UNII

06O0TC0VSM

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Fucoxanthin, (3s,3's,5r,5'r,6s,6'r,cis)-isomer

2. Fucoxanthin, (6'r,13'-cis)-isomer

3. Fucoxanthin, (6'r,13-cis)-isomer

4. Fucoxanthin, (6's)-isomer

2.3.2 Depositor-Supplied Synonyms

1. 3351-86-8

2. All-trans-fucoxanthin

3. 06o0tc0vsm

4. Chebi:5186

5. (3's,5'r,6'r)-3'-acetoxy-5,6-epoxy-3,5'-dihydroxy-6',7'-didehydro-5,6,7,8,5',6'-hexahydro-beta,beta-caroten-8-one

6. (1s,3r)-3-hydroxy-4-((3e,5e,7e,9e,11e,13e,15e)-18-((1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene)-3,5,5-trimethylcyclohexyl Acetate

7. (3s,3's,5r,5'r,6s,6'r)-3'-(acetyloxy)-6',7'-didehydro-5,6-epoxy-5,5',6,6',7,8-hexahydro-3,5'-dihydroxy-8-oxo-beta,beta-carotene

8. (3s,5r,6s,3's,5'r,6'r)-3,5'-dihydroxy-8-oxo-6',7'-didehydro-5,6-epoxy-5,6,7,8,5',6'-hexahydro-beta,beta-caroten-3'-yl Acetate

9. Fucoxanthin, All-trans-

10. Ccris 4055

11. Unii-06o0tc0vsm

12. Brn 0073179

13. Fucoxanthol

14. Cis-fucoxanthin

15. (3s,3's,5r,5'r,6s,6'r,8'r)-3,5'-dihydroxy-8-oxo-6',7'-didehydro-5,5',6,6',7,8-hexahydro-5,6-epoxy-beta,beta-caroten-3'-yl Acetate

16. .alpha.-carotene, 6',7'-didehydro-5,6-epoxy-4',5,5',6,7,8-hexahydro-3,3',5'-trihydroxy-8-oxo-, 3'-acetate, All-trans-

17. Beta-sitosterol 45%

18. Fucoxanthine - 50%

19. Fucoxanthin [mi]

20. Fucoxanthin [inci]

21. Schembl37284

22. Fucoxanthin [who-dd]

23. 5-18-04-00673 (beilstein Handbook Reference)

24. Beta,beta-carotene, 3'-(acetyloxy)-6',7'-didehydro-5,6-epoxy-5,5',6,6',7,8-hexahydro-3,5'-dihydroxy-8-oxo-, (3s,3's,5r,5'r,6s,6'r)-

25. Mls000728353

26. Fucoxanthin, Analytical Standard

27. Chembl1575074

28. Sjwwtrqnnrntpu-abbnzjfmsa-

29. Dtxsid901031617

30. Fucoxanthin, Carotenoid Antioxidant

31. Hms2219k22

32. Fucoxanthin (from Wakame) (brown Seaweed) (undaria Pinnatifida)

33. Hy-n2302

34. Zinc8221218

35. Lmpr01070300

36. Akos037514648

37. Cs-8167

38. Ncgc00247434-01

39. All-trans-fucoxanthinall-trans-fucoxanthin

40. As-56344

41. Smr000453597

42. Xf162694

43. C08596

44. Q96385

45. 351f868

46. All-e-(3s,5r,6s,3's,5'r,6'r)-fucoxanthin

47. Fucoxanthin Solution, 1 Mg/l In Ethanol, Analytical Standard

48. (1s,3r)-3-hydroxy-4-((3e,5e,7e,9e,11e,13e,15e)-18-((1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaenylidene)-3,5,5-trimethylcyclohexyl Acetate

49. (3s,3's,5r,5'r,6s)-3'-acetoxy-5alpha,6alpha-epoxy-3,5'-dihydroxy-8-oxo-6',7'-didehydro-5,6,7,8-tetrahydro-beta,beta-carotene

50. (3s,3's,5r,5'r,6s,6'r)-6',7'-didehydro-5,6-epoxy-4',5',6,7-tetrahydro-3,3',5'-trihydroxy-.beta.,.beta.-caroten-8(5h)-one

51. (3s,3's,5r,5'r,6s,6'r,8'r)-3,5'-dihydroxy-8-oxo-6',7'-didehydro-5,5',6,6',7,8-hexahydro-5,6-epoxy-beta,beta-caroten-3'-

52. .alpha.-carotene, 6',7'-didehydro-5,6-epoxy-4',5,5',6,7,8-hexahydro-3,3',5'-trihydroxy-8-oxo-, 3'-acetate

53. .beta.,.beta.-caroten-8(5h)-one, 6',7'-didehydro-5,6-epoxy-4',5',6,7-tetrahydro-3,3',5'-trihydroxy-, (3s,3's,5r,5'r,6s,6'r)-

54. 6',7'-didehydro-5,6-epoxy-4',5,5',6,7,8-hexahydro-3,3',5'-trihydroxy-8-oxo-.alpha.-carotene 3'-acetate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₄₂H₅₈O₆
Molecular Weight	658.9 g/mol
XLogP3	8.1
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	12
Exact Mass	658.42333957 g/mol
Monoisotopic Mass	658.42333957 g/mol
Topological Polar Surface Area	96.4 Å²
Heavy Atom Count	48
Formal Charge	0
Complexity	1530
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	7
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1